September 29, 2023 Things to Do


Culpeper, Virginia is the perfect place to spend a fall weekend, leaf peeping, exploring local farms, enjoying fall festivals, listing to live music at a local brewery or exploring downtown shopping and dining. Here are just a few reasons to plan your fall getaway to Culpeper, VA today.

Below is a listing of upcoming events, festivals, and activities in Culpeper, Virginia this month. Events include concerts, festivals, and family-friendly activities for the community. 

To view and sort events by date, visit: VisitCulpeperVA.com/events.

Fall Festivals and Events

10/7 Fall Festival at Belmont Farm Distillery – Come join us for our first annual Fall Festival. Live music by Steel Grey Band. Food for sale by The Knights of Columbus. We’ll have Vendors and a Corn hole Competition. Tours, tastings, and a FREE Cocktail also available! Mark your calendars and come celebrate with us on the farm.

10/13 Terror-arium Workshop at Botanical Dwellings – Spooooooookkyyyyyyyyy! Tis the season for creepy crawlys and terror galore. Join us at the start of the spooky season for this terror-ific workshop!

10/14 6th Annual Crafts Meow Falliday Craft Show – Fall craft festival highlighting local vendors, food, raffles and fun! Proceeds to benefit the kitties of Forgotten Felines of Culpeper. Forgotten Felines of Culpeper is a 501(c)(3) nonprofit rescue.

10/14 Graffiti House Paranormal Events Spirit Night – Join the team from Culpeper Paranormal Investigations from 5pm-9pm for an open-house event with tours of the location, evidence review from various places that we have investigated, equipment displays and more. Free admission, kid friendly.

10/22 Doggy Costume Contest at Old Trade Brewery & Cidery – Join Old Trade and the K9 Caring Dog Angels for our first Doggy Costume Contest! We will have prizes for the 1st, 2nd and 3rd place costumes!

10/23 Fall Festival and Craft Fair at Mountain Run Winery – Come celebrate the harvest with us!

The craft fair is going to be great this year. We will have more than FOURTY local craft vendors lined up, live music, moon bounce, playground and of coarse wine and beer!

10/28 – 10/29 Just Here for the “Boo”ze Halloween Weekend at Mountain Run Winery – Come out Halloween Weekend at Mountain Run Winery and enjoy delicious wines, beers, ciders, and music. And be sure to bring the kids for a fun cauldron hunt to get candy!

10/28 Trunk-or-Treat at PATH Recreation & Fitness Center – Stop by for a family-friendly time with treats, music, games & Halloween fun!

10/31  Culpeper Downtown Trick or Treat – Culpeper Renaissance Inc. and Culpeper Downtown Businesses invite all the little ghouls and goblins for a fun and safe trick or treating experience in Historic Downtown Culpeper from 5pm – 6pm on Monday, October 31st!

More October Events

10/7 Culpeper Cycling Century & Tour 2023 – Come join us for the 16th Annual Culpeper Cycling Century & Tour on Saturday, October 7, 2023 and experience a fun and intimate ride on your choice of 30, 60, or 100 miles of paved roads in the scenic Piedmont Region of Virginia.

10/7 Broken String Bluegrass Festival at Death Ridge Brewery – 3rd Annual Broken String Bluegrass Festival! Doors open at 11am for a full day of the best in bluegrass, kicking off at 12pm! Music by Shannon Bielski and Moonlight Drive, Hammaville, Unspoken Tradition, Junior Sisk, and Lonesome River Band. Local food trucks Talk of the Mountain Crab Cakes & More and Graze to Griddle on site!

10/9 – 10/15 Culpeper Downtown Restaurant Week – It’s time to prepare your taste buds & appetites for Culpeper Downtown’s  Restaurant Week, the best way to try something new or enjoy an old favorite—while supporting our downtown restaurant community! Break out of the typical work-week patterns and share a meal with family and friends.

10/14 Children’s Day at the Park – Yowell Meadow Park – Enjoy free kid-focused activities, music, vendors, crafts, bouncy house and more.

10/21 Hop N’Hog Culpeper Block Party & BBQ Competition – Enjoy $3 BBQ samples, unlimited beer tastings, bourbon samples, live music, food & artisan vendors, adult games, a kid’s area and more on Saturday, October 21, 2023, from 12pm to 5pm, in Culpeper Downtown’s historic Depot District. Did we mention the best local and regional BBQ around, with a competition to boot!

10/21 Car, Truck, Tractor, and Motorcycle Show 2023 – Show will run from 10a-2p. Lots of prizes and trophies to be given away during the show. All proceeds of this car show go towards the Brandy Station Volunteer Fire Department!